How a Menswear Guy Gets Dressed for New York Fashion Week: Men's

At the start of NYFW:M's second season, we examine what goes into the wardrobes of America's most well-dressed dudes.
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Maura Brannigan
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At the start of NYFW:M's second season, we examine what goes into the wardrobes of America's most well-dressed dudes.
Guests before Etudes's fall 2016 show during Paris Fashion Week: Men's. Photo: Edward Berthelot/Getty Images

Guests before Etudes's fall 2016 show during Paris Fashion Week: Men's. Photo: Edward Berthelot/Getty Images

For editors accustomed to the womenswear market, New York Fashion Week's inaugural men's showcase was a delight. With long, hectic days and far-flung show locations, NYFW isn't always so enjoyable — but the brand-new menswear offshoot was something new entirely. Between its tasteful marketing and thoughtful venue proximity, the four-day period featured a much more relaxed environment than the women's week. (It didn't hurt, either, that nicely coiffed guys spent the week wandering the city in sneakers so good, they made our heads spin.)

We learned fairly early on that NYFW:M's low-key attitude was also well-represented in the event's street style scene. But to call it a "scene" is, perhaps, a bit of an overstatement; where much of the women's machine still runs on "peacocking," the men's shows were different. There were no Chanel hula hoop bags (that we saw, at least) at NYFW: M — just a bunch of dudes in well-tailored pants who understood the concept that less is more.

Generally speaking, street style serves a different purpose at NYFW:M. For both women and men, trends on the street are influenced by what appears on the runway; as long as the men's fashion industry continues to prioritize practicality, fit and tailoring, so too will the editors, bloggers and buyers sitting in the front row.

This, in turn, can become quite homogenous. Matt Sebra, GQ's digital style director, describes the February season as being "one giant coat show." "[Coats are] that one thing that really attracts street style photographers," he says. "Are you wearing a giant shearling? Do you have a sick moto jacket? Just based on the fact that it's cold out and you're going between shows, you don't really see anything that's under there."

How might a show-goer, then, exhibit his own enviable personal style beyond what's worn on top? "It's a lot more about details," says freelance writer and former GQ editor John Jannuzzi. "Men's clothes, in general, lack the brightness, the color and a lot of the architecture of women's clothes. So in that respect, it's a challenge to find what's actually unique in a sea of guys wearing nice coats." By nature, menswear encourages what Lawrence Schlossman, brand director at Grailed.com, calls "a more approachable way of getting dressed to begin with." He says: "That's what most menswear guys are wearing Monday through Friday — so when Fashion Week comes around, it's very easy to transition that same trendy look and bust out a couple interesting flourishes to elevate it."

Models exiting Lemaire's fall 2016 show during Paris Fashion Week: Men's. Photo: Melodie Jeng/Getty Images

Models exiting Lemaire's fall 2016 show during Paris Fashion Week: Men's. Photo: Melodie Jeng/Getty Images

Where women's accessories can be larger than life, Jannuzzi characterizes the men's versions as being smaller, more detail-oriented. "The flock certainly gets off on the little things — pins (my own favorite), scarves, gloves, absurd pocket squares — and some guys just straight-up wrap themselves in blankets." 

Isabel Wilkinson, T Magazine's senior online editor, understands that those accessories can be more than an indicator of one's personal style. "There are all these cues men take that are ways of secretly indicating that they're stylish to each other," she says. "It feels like they're sending signals to an inside audience."

But it's shoes, the immovable pillar of men's streetwear, that hold the most sartorial gravitas. "A lot of guys build from the shoes up," Skylar Bergl, style news editor at Complex, tells me when asked how he builds his outfits. "The first place we look, as men, is the sneakers and the coat. That's all that really matters. If you have a really dope coat or really dope sneakers, people will notice."

Beyond sneakers, Schlossman mentions the current voguish appeal of ankle boots — Chelsea boots, especially — a trend he expects to reach saturation this week; we have celebrity influencers like Kanye West and Harry Styles to thank for that. "While you might normally see a dude wearing boots — it could be Timberlands; it could be some fancy English ones with broguing — you do see a specific type of trend boot during Fashion Week," he says.

Schlossman then compares menswear's current fixation with Chelsea boots to that of a woman's "It" bag. "During these big moments like Fashion Week, you're going to see more Chelsea boots because they're trendy and they're this 'hot' thing," he says. "If you've acquired that in the past year of the trend's life cycle, you're going to bust it out and show it off when you know there's going to be cameras around."

Outside Ricardo Seco's spring 2016 show during New York Fashion Week: Men's. Photo: Daniel Zuchnik/Getty Images

Outside Ricardo Seco's spring 2016 show during New York Fashion Week: Men's. Photo: Daniel Zuchnik/Getty Images

Trends may ebb and flow based on what is being shown during any given season — but during women's Fashion Week, they're fairly easy to identify. Be it a head-to-toe look courtesy of Moschino or a Rosie Assoulin-esque off-the-shoulder blouse, street style stars are often repetitions of one another, pulled straight from the pages of a lookbook, a popular Instagram image or even a direct pull from the runway. For men, such cookie-cutter peacocks may be less common, but that certainly doesn't mean they don't exist.

"In my mind, there's not really an equivalent across genders between women wearing some crazy stiletto with a gun as the heel to a guy's footwear," says Bergl. "It takes a different form of some type of shoe that's hard to get and really rare or really expensive."

In 2016, street style extremists take many forms, most notably what Schlossman refers to as Yeezy Season cosplay. "You can appreciate those clothes, but nobody is going to wear an oversized bouclé sweatsuit with the sweats tucked into the [Yeezy 950 Boots] and some type of giant, exploded camel parka," he says. "Now that [West] is, to some extent, a successful fashion designer, his influence, stylistically, is peak."

But subtlety is king, and menswear editors may question your status should you waltz into a show dressed head-to-toe in a single brand. "There's a weird attitude between the people who do want to get photographed and the people who are really in it for work," explains Bergl. "Then there's a further divide between people who want to get photographed, but don't go over the top with it, and the people who do really go for it." It's this latter category that will induce a shrug from onlookers. "They'll get photographed, if that's their hope. They can then post it on Instagram and tag whomever photographed them and have a nice little moment in the sun to themselves," he says. "There's always going to be that person. Someone has to do it, right?"

As Schlossman sees it, peacocking has a much more natural place in the women's pecking order. "I get Anna Dello Russo serves a function and she has earned the right to serve this function that — at least, in the superficial sense — someone can say, 'You were here. You came to my show.' She can then say that she was there," he says. "It's a very symbiotic thing."

Nick Wooster outside Armani's fall 2016 show during Paris Fashion Week: Men's. Photo: Christian Vierig/Getty Images

Nick Wooster outside Armani's fall 2016 show during Paris Fashion Week: Men's. Photo: Christian Vierig/Getty Images

Nickelson "Nick" Wooster, a 55-year-old menswear icon, is the singular exception to that rule. Now a self-described "free agent," Wooster has worked with such powerhouses as Calvin Klein and Thom Browne, as well as Barneys New York and Bergdorf Goodman. With more than 575,000 followers on Instagram and a slew of fan-made Tumblrs dedicated to his likeness, Wooster is the clear men's equivalent to Dello Russo, though on a smaller level. "[Wooster] is the highest of influencers on our side, and even he's pretty low-key about it," says Bergl. "It's a very different scale."

Women's Fashion Week is in need of an overhaul, and the Council of Fashion Designers of America is already taking action to give it the revamp it demands. No matter how the event may change in the future, street style will remain a crucial element. Should NYFW take on a more consumer-facing approach, as has been discussed, will its street style develop into a more toned-down men's model?

Wilkinson broaches this topic, explaining how she's felt trends shift away from what she calls "dressing for the Instagram" during the winter months. "It reached a peak a few years ago in the women's arena where dressing to be photographed felt like it was hitting a fever pitch." But she recalls a particularly ruthless 2014 storm that forced showgoers to choose between snow boots and exposed legs; many elected for the former. "I wonder now if the pendulum has swung in the other direction in favor of understated, more practical, clothes that can get you through a full day of shows in the middle of the winter."

While this pattern of dress may not make for the most visually stimulating street style photography, it does embody a deeper command of fashion as a whole. "It should take you five minutes to notice a well-dressed man," says Sebra. "A lot of times, the louder guys are the ones who get picked out. But if you were there in real life and saw people entering and exiting a show, there's tons of really well-dressed men. You might see [looks that are] more classic or traditional, but what's most interesting is looking at the finer points of what they've put together and how they've put it together."

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This story has been updated to specify Wilkinson's quote on the evolution of "dressing for the Instagram."